|Day Available||Day 2|
|Location||Main Building: Top floor, right side from Miss Danvers' office, further away than the Biology classroom, next to the Music classroom|
Art plays out much like the 1980s arcade game Qix; Jimmy must guide a pencil around a rectangular playfield with a background designed to look like brown paper. He must use this pencil to mark out areas by drawing rectangles with it. Each time he completes a rectangle, inside it the background disappears and an image of Ms. Philips sitting on a sofa appears beneath it. Once 80% of the image is revealed, the stage is won.
Jimmy has 3 lives in total. While trying to complete the image, he must dodge three kinds of enemies. Pairs of scissors travel around the border and the lines Jimmy draws; erasers travel across all unrevealed areas in diagonal lines. If either kind hits either the cursor or any part of an uncompleted rectangle, Jimmy loses a life. As Jimmy passes Art classes, the enemies become faster and more numerous. Firecrackers only appear in the last level; they sit in the center of the stage, eventually exploding and shooting debris around the playfield. Being hit by the debris loses Jimmy a life. Enemies can be defeated by trapping them inside a rectangle, but trying to do this is risky since if Jimmy doesn't complete the rectangle in time, the enemy will hit the line he's drawing and he'll lose a life.
There are three powerups as well - one completely freezes the enemies, one slows them down, and one speeds the pencil up. They can be collected either by running into them, or by trapping them inside a rectangle.
Completing art class unlocks Jimmy's ability to kiss other students. It also improves the quality of his pick-up lines. Most of the kissable girls will accept either flowers or chocolates, but Eunice only accepts chocolates. In Scholarship Edition, all the kissable girls only accept flowers, whereas Eunice only accepts chocolates. The kissable boys will always request flowers from Jimmy prior to kissing him, even if Jimmy completes Art 5.
Receiving a kiss refills Jimmy's Health Bar to fuller than 100%, regardless of where it was before he received the kiss. Exactly how much it refills depends on how many Art classes Jimmy has passed.
|Art 1||Light kiss on the lips||125% health|
|Art 2||Hug and kiss||150% health|
|Art 3||Hug and prolonged kiss||175% health|
|Art 4||Full make-out||200% health|
|Art 5||Full make-out (same as Art 4)||Girls no longer request a gift|
Art set trophy